you know, when I first started out I had the same problem. Including podcasts, my itunes library is well over 4,000 "songs" It's about 3,000 songs and about 1,000 podcasts. Getting that organized into winamp/roadrunner is something that challenges me to this day. I don't really have an answer for you, other than to just keep working on it until you find something that works for you. I ended up seperating out the podcasts into their own folder in "my documents" and using the multiple audio location file that you can create to see them inside rr. I then reorganized most of my music into "my music" folder by artist and left the onesies and twosies in the itunes folder as "all music"